73153-56-7Relevant articles and documents
Radical Pair Mechanism in the Aromatic Rearrangement of O-Alkylsulfinyl-N-phenylhydroxylamines
Heesing, Albert,Kleine Homann, Walter,Muellers, Wolfgang
, p. 152 - 164 (2007/10/02)
O-Alkylsulfinyl-N-benzoyl-N-phenylhydroxylamines (3) rearrange at -70 degC to give sulfonamides 4, o-sulfones 5, p-sulfones 6, and o-sulfonates 7.These reactions proceed intramolecularly via the radical pair 13 by -, - and -shifts in both radicals as proved both by experiments with 18O-indicated N-benzoyl-N-phenylhydroxylamine (1) and by strong 13C-CIDNP effects.The third oxygen in the o-sulfonate 7 is donated by a second molecule of the educt 1.